Abstract
An eco-friendly preparation method for the novel bioactive imidazolium ionic liquids halides (ILs) was developed under microwave-assisted conditions. Synthesized ILs were characterized by spectroscopic techniques. Selected ILs were investigated for their antimicrobial activity against highly resistant Gram-positive and Gram-negative bacterial strains. Overall, 3-(2-chlorobenzyl)-1-phenethyl-1H-imidazol-3-iumchloride (4) showed high antimicrobial activity against the Staphylococcus aureus strain in the inhibition zone tests and displayed low MIC and MBC levels against almost all tested bacteria. Furthermore, the ILs were screened in vitro against human hepatocellular carcinoma (HepG-2), human breast adenocarcinoma (MCF-7), and human colon carcinoma (Caco-2) cell lines. The screening results showed excellent to moderate anticancer activity across the ILs. Among the synthesized ILs, Overall, 3-(2-chlorobenzyl)-1-phenethyl-1H-imidazol-3-ium chloride (4) and 1-phenethyl-3-(3-phenoxypropyl)-1H-imidazol-3-ium bromide (7) were found to exhibit the most promising ant proliferative effects and had the lowest IC50 values. The docking study suggested strong interaction of ILs with DNA with binding energy ranging from −4.9 to −4.1 kcal/mol. ILs 4 and 7 were most strongly bonded with −4.9 and −4.8 kcal/mol binding energy; confirming in vitro anticancer results.
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•Economic microwave synthesis of novel phenethylimidazolium based ionic liquids.•Antimicrobial activity of the synthesized ILs against resistant Gram-positive and Gram-negative bacteria.•Anticancer screening of the synthesized ILs against MCF-7, HepG-2 and CACO2 cell lines.•In-silico physico-chemical analysis to predict molecular properties.•Docking with DNA to determine working mechanism.